


Red Lipstick And A Winchester

by ShadowBiscuit



Category: Supernatural
Genre: Anal Fisting, Aw yes Sam in a skirt, Begging, Bottom Sam, Crossdressing, Crossdressing Sam, Date Rape Drug/Roofies, M/M, Makeup, Pink Panties, Sex on a Car, Top Dean
Language: English
Status: Completed
Published: 2015-07-20
Updated: 2015-07-20
Packaged: 2018-04-10 07:36:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 9,265
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4383035
Author URL: https://archiveofourown.org/users/ShadowBiscuit/pseuds/ShadowBiscuit
Summary: <blockquote class="userstuff">
              <p>It was the hair. Always with the hair. So of course, when one of them had to dress up as a girl, it had to be Sam.<br/>Getting to the bar, serving as bait for the monster they were here to hunt, then knifing that son of a bitch. That was supposed to be the plan...</p>
            </blockquote>





	1. The Makeover

“I hate you,” Sam grumbled, taking another swig from his beer because he needed to be drunk for this. He glared at Dean, who was sitting next to him and grinning like the smug bastard he was, enjoying his own bottle of beer, his legs up on the table, looking calm and relaxed. Sam hated it, then when his brother snatched his bottle out of his hand, Sam’s glare intensified. “C’mon!”

“Hey, you shouldn’t get drunk, at least not yet. A girl can never be too careful, right?” He winked, earning Sam Winchester’s famous bitchface.

“Shut up. I still don’t get why it has to be me. And I swear, if you’re gonna say something about my hair, I’ll sucker punch you. You could just as easily wear a damn wig, not to mention that you’re shorter than me,” Sam growled, crossing his arms and if someone who didn’t know what this was all about would have been watching, they’d have thought that Sam was sulking, like a little kid.

As it turned out, someone _was_ watching.

“What’s the pouty face for, Sam?” A cheery voice came from the entrance of the bunker, and soon the hunters were greeted by one of their friend who was still alive. “What’s up bitches?” Charlie smiled at them, limping over to her friends. Sam and Dean both got up from their chairs and hugged her. They missed their friend.

“Charlie, hey. How are you?” Sam asked, smiling widely, his friend just waving a hand dismissingly.

“Been staying out of trouble, if that’s what you want to know. Now, what was the SOS call for? And more importantly, what do you guys want to do with all the makeup and cosmetics that you had me bring with me?” she asked, raising an eyebrow as she put her bag on the table and looked expectantly at the hunters.

Sam sighed and was about to answer when Dean spoke before him. “Charlie, what’s up with your leg?” he asked, nodding at the hospital walking stick she was carrying under her arm.

“Oh, this?” Charlie smiled. “Just a smaller hunt gone wrong, nothing to worry about. But nice try changing the subject.”

Dean grinned and pulled the bag towards him, unzipping it and taking out a red lipstick. He raised it to Sam’s mouth, his grin widening dangerously. “Hey Sam, I think this color suits you.”

Sam let out a long, annoyed sigh and slapped his idiot brother’s hand away, motioning to Charlie’s broken leg. “That’s part of the reason we called you here. At first, we thought that we could ask a favor from you, but then thought against it. We used you as bait once, and it didn’t end well. Then we got another idea, but we still needed you, so here you are…” Sam paused, a little hesitant and clearly not wanting to get to the point, so Dean helped him out.

“The short version is we’re hunting a Mayan Goddess, who kidnaps women who have all been to a bar called The Cheetah Pub, then impregnates them and kills them after she eats the baby. Nasty fucker, so we thought of luring it out. And, well, we kinda need bait for that. Woman bait,” he explained, before glancing at an annoyed-looking Sam and wiggling his eyebrows.

“No way.” Charlie covered her mouth to stop herself from laughing. “Sam? So I’m going to turn you into a girl? Oh my god, this is going to be so much fun. Sorry Sam.”

“But why me? Why not Dean? I mean, it’s not like he’s manlier than me!” Sam practically whined, hating the fact that even Charlie was enjoying his suffering.

“Sorry, man, but I clearly am. But hey, at least you won’t have to wear high heels. You’re already tall enough.” Dean chuckled, then made the right decision to step away from his little brother who really looked like he was about to punch him in the face.

“Dean’s right. Kind of. You would be a much better girl, Sam. And it’s just going to be for a hunt, right? You guys can just forget this ever happened after you caught the monster and iced her. Come on, Sam, it’s going to be fun, I promise. I’ll make a hotty out of you,” Charlie said excitedly, Sam clearly being the only one who wasn’t enthusiastic about the whole thing. Then to his horror, she added, “Oh, and we’ll also need some clothes!”

Sam looked at Charlie, then at Dean, wide eyed and shaking his head. “No. No way. I’m not dressing up— I won’t crossdress!” he objected, but knew that his word against the two smiling evils’ would be useless.

“Okay, then I’ll prepare Sammy for the makeup session, and you head down to the small boutique thing that’s not too far from here,” Dean said excitedly as he ignored Sam’s protests, starting to drag the taller hunter to the bathroom.

“Whoa wait, wait! You’re going to make Charlie do the shopping with her broken leg?” Sam asked incredulously, but when he looked at the girl, all she did was smile.

“Don’t worry, it doesn’t hurt anymore. And, anyway, Dean wouldn’t know what to buy. But I’ll need him to give me your three sizes,” she said with a grin, and when both brothers frowned in confusion, Charlie rolled her eyes. “Bust, waist and hip measurements, dummies. Oh, and I’ll be taking your money. Just in case.”

“In case of what? You see the dress of your dreams?” Dean scoffed, then immediately stopped smiling when he saw Charlie glaring at him.

“Yes, for example,” she said, before extending her hand with her palm up, waiting until Dean finally gave up and pulled out his wallet and gave her one of their fake credit cards. “You better hope this still has enough money on it. Anyway, I’ll call you when I get there. Peace out and good measuring!” Charlie waved at them, before turning on her heel, not as gracefully as she hoped she would thanks to the cane, then was walking up the stairs and was gone.

“So…” Dean raised an eyebrow, a grin tugging at the corner of his lips. “Let’s get you measured, then.”

“I think that I can do it myself, thanks,” Sam muttered, heading to the bathroom, but before he could have locked himself in, Dean blocked the door with his feet, forcing it open and in the next moment he was inside with Sam.

“Please, it’s easier if I do it,” he scoffed, walking to the cabinet and after a few moments of searching, he took out the measuring tape with a victorious smile on his face. “Found it.”

Sam groaned in frustration as he unbuttoned his shirt and let it fall to the ground, hesitating as his hands hovered above his pants.

“What are you waiting for?” asked Dean, leaning against the sink with a hand resting on his waist. “You embarrassed in front of me? C’mon Sammy, don’t be a girl _already_ ,” he teased his little brother, making Sam glare at him before unzipping his pants and kicking them off.

“You happy now?” Sam asked, letting his arms hang lazily.

“Very,” Dean answered. “Now raise your arms and let me take your size.”

Sam sighed, rolling his eyes as he did as he was told, raising his arms and letting Dean get to work. It was pretty embarrassing, but he knew that the worst was yet to come.

He felt his big brother’s cold fingers brush against his skin, a shiver running down his spine from the touch and, surprisingly, the places Dean touched felt hot, burning even. For a split second, Sam wondered if he had a fever, but that couldn’t be it. Dean’s eyes were on his naked, except for his underwear, body, and Sam’s heart began to beat faster. He licked his dry lips and clenched his jaw, feeling the hair on his arms stand on end. As his brother moved his hands lower, Sam had to force down a gasp, and when Dean wrapped the measuring tape around his hips, the feeling as the tape grazed against his cock and Dean’s fingers on his skin had Sam pushing him away.

“Hey, chill.” Dean frowned, walking back to the cabinet and putting the measuring tape away. “I’ve got all your sizes, now all we need is—”

He was cut off by the sound of his ringtone. He grinned and said, “Speak of the devil,” before pulling his phone out of his jacket pocket, and then left the bathroom while talking to Charlie, leaving Sam alone and confused.

What the hell just happened? He watched his underwear in horror, looking at the slight bulge. Dean didn’t notice, but Sam did. He wasn’t hard, not really, but could feel something, a warmth in his stomach when his brother touched him. This has never happened before, so after a thing that could only be called breathing exercise, he forgot all about it. He was sure that it was his body’s way of telling him that it lacked physical touch. It has been a while since he got laid, after all.

He put his clothes back on before joining his brother in the main room, just in time to hear him finish his conversation with Charlie.

“No, I’m telling you we’ll need the coat. And yes, those too. Charlie, no— Listen, I said no. That’s exactly why we need the coat. Okay…okay. Right, hurry up.” Dean sighed, apparently done with the phone call as he tossed his cell phone on the table, then flopped down in one of the chairs and went back to drinking the beer he stole from Sam. Upon noticing his little brother, he looked at him, grinning from ear to ear. “Guess what Charlie wanted to buy you?”

“Do I wanna know?” Sam asked as he walked to the table and leaned against it, eyeing the bottle bitterly. Dean shook his head as he took another swig, then laughed.

“No man, you don’t. But I’m still gonna tell you. A fucking _bra_. She wanted you to have breasts,” he said, grinning even wider as he saw the look of horror on his little brother’s face. “Don’t worry, I talked her out of it, though the idea sounded pretty fun.” Dean winked.

“If it’s so fun, then you wear it,” Sam snapped, grumbling like an old man. Seriously, what was wrong with Dean? He was going to make his big brother pay for this, Sam promised himself.

It didn’t take too long before Charlie came back, holding two shopping bags full of mystery things. “Alright miss, let’s go to your room and get you changed. Dean, you stay here so that you don’t disturb us. And no buts,” she said, and Dean just nodded, that stupid smile never leaving his face as he watched Sam leave the library with Charlie following him close behind.

Reaching his room, Sam opened the door for Charlie and let her in first, before walking in and closing it. “I’d lock that, if I were you. You really don’t want Dean walking in on this,” she told him as she pulled out a black skirt from one of the bags and held it up for Sam to see.

“You… Are you kidding?” Sam stared at the short, ragged skirt in terror. But Charlie shook her head and gently placed the skirt on the bed.

“Okay Sam, time to strip. Don’t worry, I won’t look.” She smiled and handed the bigger shopping bag to Sam before walking around the bed and sitting down on the side, facing the wall with her back to the hunter. “That bag has all your clothes in it, except the skirt that’s on the bed. Hurry up, I want to see how you look like.”

“Damn it,” Sam muttered under his breath, let out a long sigh, then just poured the contents of the bag on the bed.

The first thing he recognized made his blood run cold.

It was a pair of pink panties, with a small black ribbon on each side of the waistband. On a closer look, they appeared to be made out of satin and, sure enough, when Sam took them in his hands, they felt…well, satiny. “Charlie?” Sam looked at the girl, wide eyed.

When she turned her head around, she made a face like a kid who’s just been found out, and smiled. “It’s…I thought that if you’d wear that, you could feel more like a woman. You know, play the part more convincingly? No?”

“No. I don’t need to feel like one, just look like one,” Sam said, frowning and looking at the panties as if they could come alive any second and attack him and his manliness. Mostly his manliness.

“Come on, Sam! Just wear them. It’ll be fun, and nobody will ever know!” Charlie urged him, putting her hands together and begging the hunter. “Please?”

Sam stayed silent for a long moment, glancing from his friend to the satin panties, then let out a defeated sigh. “Alright, fine. But you can’t tell Dean, can’t tell anyone, ever, alright?” he said, Charlie nodding quickly and beaming up at him.

“Awesome!” She smiled widely, then turned back to the wall and waited for Sam to change. Sam felt uneasy as he pulled his shirt off and got rid of both his pants and underwear.

He was now standing stark naked and had to put those pink atrocities on, telling himself that it was okay, that no one, except for Charlie of course, was going to know. And aside from him, no one will see him in those panties, ever. So with that thought in mind, Sam pulled on the satiny panties and damn, did they feel smooth against his skin. It actually felt really good, and comfortable, though it was a little tight around the area of his cock, but he could get used to that. He smirked to himself as he put the skirt on next, which was pretty small, the end of it barely reaching his knees. Sam looked for a shirt next, and soon found it under the coat that was surely meant for him, too.

The coat was a long, brown fur coat, and the shirt was dark gold and looked pretty complicated. It looked like a tank top, but at the front there were many horizontal line shaped holes going down, smaller and smaller, until they stopped around the area where Sam’s stomach would be. Sam hesitated, not really sure that wearing something like that would be a great idea, but he already had pink panties on, so what the hell. He pulled the top on and looked at the long stockings, the only thing left aside from the coat on the bed. They were also black and a little transparent, though there was a large line at the top of the stockings which was completely black and not transparent at all.

Well, at least they weren’t strap-on stockings.

Sam reluctantly put them on, then after putting the flat black shoes on—that were surprisingly comfortable too—and looking himself over in the mirror, he cleared his throat.

“Okay, uh, you can look now,” Sam mumbled and suddenly felt a bit sheepish as Charlie turned around and smiled broadly.

“Sweet mother of Rowling, you look…” She trailed off, looking pretty stunned and maybe even shocked, staring at Sam and making him feel more and more uncomfortable by the second.

“Weird? Horrible? Yeah, I know,” Sam said, chewing his lower lip as he played with the end of his ragged skirt.

“I was thinking more along the lines of hot and sexy and just, wow. If I was into dudes, I’d totally bang you right now.” She grinned, making the hunter uncomfortable.

“Well, thanks I guess,” he finally said with a smile, and looked at the coat. “Should I put that on too?”

“No, no. Not yet. First, I’m going to turn you into an even hotter babe.” Charlie clapped her hands together and pointed at the end of the bed. “Okay, sit.”

Sam scratched his head nervously, but did as he was told, taking a place at the end of the bed while Charlie pulled a chair in front of Sam and grabbed the second, smaller, shopping bag and her own bag, before taking seat in front of the hunter. “Alright, I’m going to start with your hair. Oh wait…” She frowned, then shook her head. “Not good. I need you to shave.”

“What? I can’t go out of the room like this!” Sam protested, looking terrified all of a sudden.

“Oh, please. You’re going to have to get out of the room sooner or later, anyway. Don’t worry, I’ll stay with Dean while you shave your face, and you can even call me on my phone when you’re done. Deal?” she asked, raising her eyebrows and, after a moment of silence, Sam nodded and sighed an “Okay.”

“Great!” Charlie smiled, then left the room.

Sam followed soon after, walking to the bathroom that was thankfully pretty close and took the shaving foam out of the cabinet. He sprayed a generous amount in his palm and rubbed it on his chin and lower part of his cheek, before taking out the razor. It only took him a few minutes to shave his face and, after washing the remains of the foam off, he dried his face and was about to walk back to his room, but stopped. He looked at himself in the mirror, then lifted one of his arms. He thought about shaving his armpit too. Girls usually did that, after all. But Sam wasn’t a girl, he had to actually remind himself, he was just dressing up as one. However…the more he believed it, the more the monster was going to believe it and fall in their trap. So, he also quickly shaved his armpits before finally going back to his room, and called Charlie.

Soon enough, she was back and gave Sam a thumbs up. “Looking good. Now, get back on the bed and let me work my magic on your hair,” she said cheerfully as Sam took his place at the end of the bed, Charlie crawling and kneeling behind him.

“You’re not going to braid my hair, are you?” he asked a bit worriedly, watching as Charlie took out a brush from her bag.

“Oh, I’m tempted, but no. Your hair’s going to be pretty simple. I’m just going to brush it and style it a little, nothing big,” she assured the hunter, and then began brushing his soft hair until it was smooth. “I’ve always wanted to play with someone’s hair. Never thought that it’d end up being yours, but I’m not complaining.”

Sam smiled but stayed silent while Charlie made sure his hair looked perfect, then got off the bed and began going through her bag. After a few seconds of desperate searching, she finally found what she was looking for, and pulled out a smaller bag. “My makeup bag. Time for you to look pretty. Not that you don’t already look good but, you know.” She winked, then sat down the chair facing Sam and leaned forward, tucking some stray strands of hair behind the man’s ears. “Alright, close your eyes and don’t you dare open then until I’m done, capiche?” she said, to which Sam nodded, still smiling as he closed his eyes.

He had no idea what Charlie was doing, but could feel it. He felt something cold against his cheeks and whole face in general, but he didn’t really need to guess what it was, because he soon heard his friend’s voice, explaining what she was doing. “Okay, so now I’m applying some foundation. Your skin should look nicer after this and some powder which I’m putting on you right…now.” She paused, and sure enough, Sam felt something soft on his skin, like a cloth. She did something else, around his cheeks, then said, “Alright, put some blush on that pretty face of yours too. Now, open your mouth, but just a bit. We’re gonna use the lipstick, a nice shade of red.”

Sam opened his mouth and felt something press, then smear across his lips. He really was going to do this. He really was going to look like a damn woman after Charlie’s done. He was getting nervous again, but it’s not like he could’ve done anything about it, not now, it was far too late for that. He couldn’t turn back now. And, honestly, he was pretty curious about how he’d look like as a woman. Or more like a man who was wearing woman clothes and makeup.

“Okay, now a little bit of lip gloss, and…done!” Charlie said cheerfully, and Sam was about to open his eyes when she quickly made a displeased sound. “Eh eh, not yet. Sam, we still need to do the most important part—your eyes. Patience, honey.” She grinned, at least the way she talked sounded like she was grinning, then Sam felt something, like a tiny brush, on his eyelid. “Eye shadow. Makes you even prettier. And after I’m done with that, I’m going to…damn, where is it?” Sam chuckled as he heard Charlie fumbling in her bag, then she must have found whatever she was looking for, because Sam soon felt something cold and wet at the bottom of his eyelids, the part where skin met eyelashes.

“What’s this?” he asked, frowning at the odd feeling.

“Oh, it’s just some eyeliner, a liquid one. I’m sure it must feel a bit unusual but stop frowning, it makes it harder for me to beautify you,” she said, Sam reluctantly relaxing his face and letting Charlie work. It didn’t take long for her to start talking again, however this time she asked Sam to open his eyes. “I have to do your bottom eyelids too. Okay, no, I don’t have to, but I wanna, so c’mon, I don’t have all day,” she joked and Sam was smiling again as he opened his eyes, noticing how Charlie’s face lit up. “Holy Sauron, you look awesome! I can’t wait to see how the final masterpiece is going to look like!” she said excitedly, smiling ear to ear.

“Hey, I’m not some kind of art project.” Sam faked a sad pout, immediately feeling as if something was wrong. It was his lips. They felt weird, making him press them together. Charlie noticed it, but all she did was smile.

“Good thing you did that, I was about to ask. Keep rubbing your lips together, that’ll like, even the lipstick out. Anyway, now look up,” she told Sam, who slowly did so and had to fight the urge to blink or close his eyes while Charlie put more eyeliner on him. Now that his eyes were finally open, he saw how that thing looked like and it was just like some kind of pen. An intimidating looking pen. It was weird, and knowing that the black ink was on his skin now felt even weirder. Thankfully, Charlie was working pretty fast so Sam only had to wait for a minute or two before being allowed to look down.

“So, are we done?” he asked hopefully, but judging from the wicked grin on the girl’s face and the small, thick bottle-like thing she was holding, it wasn’t nearly over. Just as Sam thought, Charlie shook her head and raised the small thing. “Mascara time, my friend. Now, I want you to half close your eyes, just a bit,” she said, earning a long sigh from the hunter. Sam nodded and closed his eyes a little, as if he was squinting. He felt, and saw it a bit, too, as Charlie brushed his eyelashes with that black thing from the top and at the root of his lash line upwards, then when she was done with doing that, she did the same thing to the bottom of his upper eyelashes, as if she was stretching them slightly outwards. “Okay, look up again.” And Sam did, before Charlie applied mascara on his lower lashes. She then leaned back, most likely to admire her work, before taking something else out of her bag. “Last thing, I promise. I mean, last makeup thing.

I still have some other stuff in store for you. But anyway, close your eyes again.”

“I feel like we’ve been doing this for an hour,” Sam complained as he closed his eyes and let Charlie apply something else on his eyelids, though this time it only took a few seconds before she told Sam to open his eyes again. “So, done?”

“Yes, the makeup part is done. Want to see it?” she asked, already holding a small mirror in her hands, so of course Sam nodded. “Good! Say hello to the new you, Sam Winchester.”

He rolled his eyes as he took the mirror from Charlie, but nearly gasped when he saw his reflection. “This…this is me?” he asked incredulously as he stared at himself in the small mirror. He looked so different, and from afar, people might actually believe that he was a girl. Sam’s hair looked more beautiful than ever, even though it was kinda the same as always. A woman’s touch could make miracles. And his face, it was unbelievable. His face looked so damn smooth, his lips were a beautiful shade of red, not the too flashy but more the subtle kind, and his eyes…those were the most shocking. Were his eyes always this green and big? There was dark golden eye shadow on his eyelids, not much but just enough to be noticed, and the black mascara was simply amazing. It must have been because of the mascara that Sam’s eyes looked bigger and somehow, brighter. Speaking of bright, Sam was pretty sure that the last thing Charlie put on him was some kind of glitter because there were many sparkly dots at his eyelids. He was wide eyed from shock as he lowered the mirror and looked at an overly happy Charlie.

“So? How do you like it? A real lady, right?” she asked keenly, rubbing her palms together and it took Sam a few moments to find his voice and answer with a nod.

“Yeah. I really…look like a girl. Or at least like a cheap stripper,” Sam said, a smile tugging at the corner of his lips as he kept on glancing back at the mirror and his reflection, which he still couldn’t believe was him. It was odd, a bit scary, but he kind of liked it. Though he’d never tell anyone.

“Hey! The glitters are cool, okay? And just one more thing,” Charlie held her finger up a she pulled out a bottle from the small shopping bag and sprayed Sam with a generous amount of—

“Is this perfume?” Sam asked but he didn’t need to wait for Charlie’s answer to know that, yes, it was perfume. A really sweet one, too. And Charlie had to go ahead and empty nearly the whole bottle on him. “Damn it, Charlie.”

“What?” she asked, pouting. “Now you smell good.” She smiled, but upon seeing the expression on the hunter’s face, Charlie quickly added, “Not like you were stinking before, but you smelled…manly. Like, sweat and just, manliness. Now you smell like candy and roses. And yes, we’re done now.”

Sam let out a sigh of relief before standing up and stretching his arms and back. “Finally,” he grumbled, but soon realized that he shouldn’t be too happy just yet. He still had to enter a bar like this, dressed and looking like a woman. And also, he had to let Dean see him like this.

“Alright, let’s show the judge my work,” Charlie said excitedly as she opened the door and beckoned Sam.

He grabbed the coat from the bed and went after his friend, slowly and cautiously. When he reached the end of the hallway, he knew Dean was there, and it wasn’t like he could skip this moment or suddenly become invisible. So, after taking a deep breath, he round the corner and walked into the library where his brother was waiting.

“Here she comes.” Charlie smiled widely as Sam walked towards them, and Dean gaped at him.

His eyes were wide and his lips were parted, as if he barely managed to stop his jaws from dropping upon the sight of his little brother. Sam waited for something, anything, a sarcastic remark or a laugh, but Dean just kept on staring at him. After a while, Sam was starting to become really uncomfortable, physically feeling his big brother’s gaze on him, his eyes roaming his body and—if this wasn’t Dean or if Sam really would have been a chick—it would have seemed that Dean was undressing him with his eyes.

Finally, his brother cleared his throat and managed a cheeky grin as he said, “Well hello there, Samantha.”

Sam was tight-lipped as he rolled his eyes. He knew that Dean was going to make fun of him. Sighting, he began heading towards the garage. “If you call me that again, I’ll beat you with my shoes,” Sam huffed before disappearing behind a wall.

Dean and Charlie looked at each other, and the hunter just shrugged. “Must be that time of the month,” he said jokingly, but the smile quickly disappeared from his face when he saw Charlie’s raised eyebrows.

“Anyway…” She nodded towards the printed images of the victims. “How do you guys plan on taking this all powerful goddess out?"

“Mayan Goddess called Ixchel, and we already have a weapon. A wooden spear dipped in dead man’s blood. All we’ve gotta do is trick her into believing Sammy’s a chick, make it follow him and then we’ll ambush it, spear to the heart and done, we got ourselves a dead goddess,” Dean said and winked at Charlie. “Wish us luck.”

“Always. Be safe, okay? And don’t let anyone hit on our Samantha.” Charlie winked back and grinned as the hunter snorted, then grabbed his duffel bag and followed Sam into the garage.


	2. Can't Help Myself

**Summary for the Chapter:**

> He was already feeling uncomfortable in the bar, with all those pairs of eyes staring a hole in his ass. So it was just Sam's luck to go and get himself roofied...

They parked in front of the bar, watching as people walked in and out. It was a pretty busy night, it seemed, so at least Sam could blend in more easily.

“Go in and look pretty, okay?” Dean patted his annoyed little brother’s shoulder, before getting out of the car and following him to the bar.

Sam and Dean have been to a lot of bars before, countless actually, but never did they meet with one like this Cheetah Pub. The first thing that hit them was the smell. It was like a meth head and a prostitute had a baby, dipped it in booze and gave it to a biker gang. The whole place stunk of sweat and cheep booze, maybe even urine. Next, were the people in the bar. They were all either girls with way too much makeup and short, tight clothes, rednecks, or a mix between metal heads and those guys that you see at the door of expensive night clubs, the ones who could bend and break your arm in a blink of an eye. And finally, maybe the worst part of the whole bar was the music. If it could even be called that. It was some kind of shitty ’60 song that sounded a lot like American Pie.

“Dude, seriously, what is this place?” Dean pulled a face in disgust and felt the need to take a shower from just being in the place. “I mean, they’re playing Don McLean! Why would a Mayan Goddess frequent a place like _this_?”

“I have no idea. But the faster we do this, the faster we’re getting out of here,” Sam mumbled, glancing from side to side, suddenly feeling like all the self confidence he had before bailed on him. He really didn’t want to be here, dressed as a woman or not.

“Yeah, you got it. I’ll be standing here while you, I don’t know, do your lady thing. Good luck.” Dean winked and playfully smacked Sam’s ass, making his little brother flash a deadly glare at him, before walking to the bar. Sam made sure to walk as delicately and carefully as he could, but no matter what Dean said, he was so not going to sway his hips.

Deciding that he wasn’t going to take the risk of catching anything nasty from the suspicious looking stools, he remained standing instead and leaned against the bar.

He quickly caught the bartender’s attention, who was a middle aged man with a black goatee, with his hair slicked back. “Can I get you anything, miss?” he asked, half smirking at Sam who was having a hard time keeping a straight face. He forced a chaste smile and tucked a few strands of hair behind his ear.

“Gin and tonic, please,” Sam said in the smoothest, high pitched and girly voice he could make, and was actually slightly surprised when the guy winked at him and made him the drink. Maybe Sam could pull this off, after all.

He downed the drink rather quickly, then asked for a refill, turning around and scanning the bar. The first thing he noticed was, of course, Dean. His big brother was leaning against the wall, looking uncomfortable, though when their eyes met, Dean’s face lit up and he grinned at his brother. Sam rolled his eyes and instead went back to look for their monster. That was when he realized another thing, which was that most of the men in the bar were totally checking him out. He felt many eyes on him, even caught a guy giving him a look over before looking Sam straight in the eyes and licking his lips. That made Sam’s stomach lurch, so he quickly turned back towards his drink and downed it, though this time it didn’t go down that easily. He was starting to feel pretty drowsy, but knew that two little drinks couldn’t make him drunk. He wasn’t that big of a drinker, like Dean, but he could hold his liquor quite well, too.

Ten, twenty, then thirty minutes passed with nothing happening. Sam was starting to seriously become impatient at this point, and also a bit tipsy. The bartender seemed eager to keep the drinks coming and Sam had already lost count how many gin and tonics he drank. He was pretty sure that it was nearing double digits, though.

“What’s a pretty lady like you doing here, alone?”

He heard a deep voice coming from the stool to his right. Sam looked at the guy and had to blink several times to stop himself from gaping. The dude was even taller than him and, unlike all the other guys in this wretched place, was actually quite decent looking. He smiled at Sam and motioned for the bartender to pour him another round, and Sam couldn’t stop himself from smiling back and this time, it was him doing the checking out. The man had short, spiky blonde hair and green eyes. He was wearing a grey shirt with a black leather jacket and dark blue jeans.

Sam found him quite attractive, for _some reason_.

If he was a girl, maybe he’d even let the guy flirt with him.

But he wasn’t, so he tried sounding as sincere and polite as he could when he subtly rejected his attempts. “I’m not alone, just waiting for someone. My boyfriend will be here shortly.”

But the guy didn’t seem to back down that easily. “Really? Because from what I’ve seen, you have been sitting here alone for half an hour. Your boyfriend must be quite the douche,” he said, reaching out and running his fingers through Sam’s hair. The hunter tensed at the unwanted touch and slowly leaned away from the man.

“Uh, yeah, I just came too early. But he’ll be here, I assure you,” Sam insisted, flashing a small smile at the guy before turning his head, signaling that the conversation was over.

And it looked like he finally got the hint. “Alright, then. But if you ever change your mind, I’ll be outside,” he said, before walking away. Sam sighed in relief and grabbed the, once again full, glass in front of him.

The guy bought it for him and one last drink couldn’t hurt, right?

-

So utterly and completely boring.

Dean had to fight to keep his eyes open. He was leaning against the wall next to the entrance, but he quickly realized how stupid that was. He felt sick, and was pretty sure that his jacket would end up in the fire tonight. No other way to clean it.

They have been in the bar for at least half an hour now and still, nothing happened. Some girls checked him out now and then, even some fugly dudes, but that was all the action. And anyway, all the attention, or at least most of it, was focused on his little brother. Or in this case, sister. The amount of men and women who gave his cross-dressing brother the once-over was countless. Dean actually started counting them, but he lost count after a while, around twenty-four.

But Dean couldn’t blame them. Sammy was indeed pretty darn hot. When he first saw him after the makeover, his heart skipped a beat. He was surprised by his reaction, the way this female version of Sam managed to make him nervous and sweat. And while in the car, with his little brother right next to him, Dean thought about it. Like, really did. But after the initial thoughts of him and Sam being brothers, both of them men, even if Sam was looking more like a girl right then, and how wrong and just fucked up it was to be turned on by Sammy, Dean soon found himself thinking about other things. For example, if Sam’s lips would feel as soft as a girl’s, maybe even softer? If he’d get all flustered and blush if Dean would whisper dirty things in his ear. Or what kind of sweet sounds would Sam make if—

But no. Dean forced himself to stop thinking and imagining his little brother in some very embarrassing and downright dirty ways, and drove. He kind of had to do the same thing now, as he realized with a glance that he was hard. Damn it. Remembering his thoughts like that was a bad idea. Still, he couldn’t stop himself from watching his little brother with hungry eyes, wondering what if, just what if…

But Dean would never touch Sammy, and anyway, he was sure that the only reason for him fantasizing about his little brother was because of the clothes Sam was wearing. All that makeup and the short skirt made it look like he was a girl. So, even if right now, Dean wanted nothing more than to feel his brother’s skin on his lips, he was sure that he wouldn’t feel the same way about regular Sam. Regular, bitchy, funny, kind, sweet, amazing, sensitive but strong Sam…

Crap.

He was lusting after Sam.

Or was it…?

No, no fucking way. Dean made himself snap out of it, because he was _so not_ in love with his own brother. Nope. Not possible.

He took in a deep breath and calmed himself. He could worry about his fucked up problems later. For now, he had a job to do and a monster to kill. Dean kept his eyes on Sam, not on his ass, then saw movement to his right. A guy, even taller than Sam, went over to him and began sweet talking him. Dean frowned, and when the stranger touched his Sammy’s hair, he clenched his fists so hard that his nails left crescent shaped marks on his palms. And the worst was, Sam seemed to check the guy out. Dean let out a quiet, possessive growl, and was about to walk over and punch the guy right in the face, but Sam seemed to handle the situation well enough. The guy looked disappointed, served him right, when Sam turned away from him, then—

What the fuck?!

It was easy to miss, because the stranger’s hand moved so fast, but Dean still noticed as he poured some kind of powder in his little brother’s drink before walking away. Sam looked relieved when the guy left, and, oh no, raised the glass to his lips. Dean’s eyes widened and he fought his way through the bar before practically slapping the drink out of Sam’s hand, but it was too late. Sam drank half of it, but even that was more than enough.

“Dean? What the hell?” Sam asked, looking shocked and pretty drunk. He was frowning at Dean and glancing around the bar, obviously still thinking about their mission.

“Your drink was drugged, you blind idiot!” Dean growled, completely forgetting about the hunt, the only thing in his mind being _Sammy, that bastard drugged Sammy, is Sammy alright?_

“What?” Sam blinked lazily, looking at the broken glass at his feet then back at Dean. “Seriously? But I…oh…” His voice trailed off, a look of surprise then realization crossing his face as he grabbed Dean’s shoulders. “Dean,” he groaned, looking like he was going to pass out any second.

“Damn it.” Dean wrapped Sam’s arm around his shoulders and half dragged him out of the bar to the car, skillfully opening the passenger seat with a Gigantor leaning over him and managed to put his drugged brother into the car. He got in as well and turned on the engine, before glancing at Sam who was really looking like crap. “Sam? Sammy, fuck, are you alright?” he asked worriedly.

“Dean…” Sam leaned his head back and shrugged out of his coat and Dean noticed how gorgeous Sam’s sweaty, tanned skin looked and no, he was not thinking about this, not now, damn it. “Dean, I think this is a date drug,” his little brother gasped, before letting out a small moan.

A fucking moan.

Dean couldn’t take his eyes off Sam, his little brother making odd movements in the passenger seat, bucking his hips in the air and running his hand through his hair. “Dean!” Sam groaned, slamming his hand against the window as he leaned forward, panting. That got Dean’s attention and he quickly pulled out of the parking lot, going as fast as he could.

“Okay, just calm down. We’re gonna take you back to the bunker, and you’ll be okay. You will be just fine, little brother,” Dean said, trying to reassure his brother but himself too, at the same time, because listening to Sam’s strangled moans and whimpers, seeing him writhe in the seat from the corner of his eyes really wasn’t helping with his own fucking erection.

“Can’t Dean, fuck, it’s like a fever. I can’t— Dean, I can’t do it!” Sam whined, palming what seemed to be his bulge through his skirt, and Dean really had to control himself.

“Just a bit longer, Sammy,” Dean said, his voice low with lust as he stared ahead and tried his hardest not to succumb to his desires.

-

Hot.

Hot.

So fucking hot.

Sam had no idea what kind of drug that guy slipped in his drink, but it was doing unimaginable things to him. His cock was already aching, rock hard and straining against his panties, and his skin was burning hot. He felt like his body was on fire. He needed it, needed something and when he looked at Dean, he immediately knew what it was.

He needed Dean.

He couldn’t wait anymore, heard Dean talking to him but he didn’t listen. All he knew was that he wanted those firm hands on his body.

Now.

-

Not even five minutes have passed before Sam was _on_ him.

Dean cursed in surprise and nearly crashed into an upcoming car as Sam attacked his neck, kissing and licking and biting and moaning in his ear. They were on a deserted road and it was dark, so Dean steered the car to the right and parked it in the dirt, quickly turning his much needed attention to his whimpering brother. He didn’t care, not anymore.

Sam wrapped his arms around his neck and pulled him into a sloppy kiss, which Dean quickly dominated, licking into his clingy brother’s mouth and claiming his lips roughly. Sam was trying to climb into Dean’s lap and dry hump him, but the older hunter pulled away from him, earning a disappointed whine from Sam.

“Get out of the car,” Dean growled, his brother moaning as he scrambled out of the car and followed him to the front of the car, where he was immediately pushed against the hood.

“Dean, Dean, want you,” Sam keened, tugging at his brother’s pants. Dean took his shirt off, but left his pants on, for now, then began undressing his panting brother.

Peeling the tank top off his little brother, Dean licked his lips at the sight and didn’t any waste time before licking at all the accessible skin there. Sam leaned back on the hood of the Impala and cried out in pleasure as Dean kissed wet trails down his chest, taking his nipple between his teeth and tugging at it, moving his teeth back and forth and making the younger hunter whine in need. “More, please! Dean!” Sam arched his back as Dean sucked on his nipple while thumbing the other, before moving down to his abdomen and licked and bit at the skin there, leaving marks all over Sam’s body. He then slid his fingers under the waistband of the skirt, pulling it off and nearly gaped in shock when he saw what Sam was wearing.

“Sammy.” Dean felt his mouth water at the sight, and couldn’t help but lick along the pulsing bulge that was straining against the satin panties, making Sam sob, actually fucking sob in pleasure as he banged his head on the hood. “Fuck, can’t believe you’re actually wearing panties. You’re so fucking hot, Sammy,” he groaned, kissing and teasing his brother’s clothed cock until he was begging.

“Dean please, please!” Sam whined, bucking his hips against Dean’s mouth desperately. Dean grinned and slowly, ever so slowly, pulled the panties off, freeing Sam’s aching cock that was rock hard and leaking pre-come. He swallowed and licked up from the base to the head, placing small kisses along the shaft, drawing a choked off moan from his little brother.

“What do you want, baby brother?” Dean purred, mouthing the words against Sam’s pulsing dick and making the already desperate hunter needier.

“Please, Dean, just— fuck me, please,” he pleaded, spreading his legs for his big brother and looking at him through half-lidded, blown eyes full of lust.

And how could Dean ever say no to that?

He grabbed Sam’s hips and pulled him down, then turned the hunter around so that his elbows and chest were resting on the hood. “You look so fucking gorgeous like this, bent over and begging to be fucked by your big brother. Sammy, you have no idea how bad I want you,” Dean said, making Sam push his hips out a bit more and lower his head and wasn’t that just the best sight ever?

Dean got down on his knees, because he couldn’t miss the chance of tasting his little brother, then spreading Sam’s cheeks, he began licking at the pink pucker. Sam threw his head back and let out an especially lewd moan as Dean licked along the tight ring of muscles, then pushed his tongue inside, licking into his brother and wetting his hole with as much saliva as he could. That was all he could use as lube, after all. He soon added a finger to his tongue, moving it in and out of his whimpering brother, then withdrew his tongue completely as he added a second, then finally a third finger too, stretching his little brother open.

“More, Dean, _pleaseplease_ more, I need more!” he heard Sam moan, gasping and pushing back on his fingers. Dean chuckled lowly as he pushed a fourth finger in, but Sam was still whining and begging for more.

“Fuck, Sammy, fine, you little slut” Dean said, grinning to himself as he slid his last finger in, then after a few thrusts, he clenched his hand into a fist.

He moved his fist slowly in and out of his brother, who was practically screaming at this point, unable to even form words, just incoherent sounds. Dean kept on fisting his writhing brother, loving the sounds he was making and placing kisses on his back, his free hand stroking Sam’s tensed thighs. After what felt like an eternity, he couldn’t keep it up and pulled his fist out of his brother, Sam making a small noise at the loss, hanging his head and breathing heavily. Dean quickly pulled and kicked his pants and underwear off, spitting in his palm and slicking his dick up with saliva, before rubbing the head of his dick against Sam’s ass crack. The younger hunter let out a breathy moan and pushed back on his dick, making hopeless and needy sounds. Dean couldn’t keep up his teasing, he was way too and painfully hard now, so without further ado, he placed his hands on Sam’s waist and slid home. Pushing slowly, all the way into his brother, who let out a drawn out moan, Dean felt like he was in Heaven. One that was way better than the real thing.

He began thrusting in and out of his Sammy in a steady pace, but he soon changed it to long, slow thrusts, teasing his brother. Though as he watched Sam cry out in pleasure under him and push back on each and every thrust of his, all of his self control left him and he sped up, fucking Sam roughly and fast, somehow managing to hit brother’s prostate more times than he didn’t. Thankfully, only two cars passed them as they were having sex at the side of the road, and one of them even honked, which kind of turned both of them even more on.

Dean could tell that Sam’s orgasm was close by the way his moans became high pitched and he kept on repeating Dean’s name. And after a few hard thrust, he was coming, untouched, on the hood of the car with a scream, making Dean lose it. He only needed two thrusts with Sam’s hole fluttering around him, and he was coming too with a groan, filling his little brother up.

They lay there panting, Sam on the hood of the car and Dean on top of his brother. He slowly slid out of him, watching as his come trickled down Sam’s thigh, before he kissed his baby brother on his back, making him look at Dean and smile tiredly. He carefully straightened up and they both put their clothes back on, though Sam needed a little assistance with his. They were silent for a long while, until Dean finally neared his throat.

“Guess we’re gonna have to come up with another plan to catch our Mayan Goddess, huh?” he said jokingly, his eyes downcast. He was seriously starting to regret what just happened, guilt overtaking him. He might have just ruined their relationship, taking advantage of Sam in his drugged state like this.

“Dean.” Sam’s voice snapped him out of his guilt trip, making him look into those beautiful eyes, but instead of hatred, all he could see was love. “I know what you’re thinking, and don’t. I would have…never thought that this would happen, but I liked it. Well, more like loved it, actually,” he said sheepishly, and was Sam _blushing_?

Dean couldn’t stop the wide smile that spread across his face, and grabbed the back of his littler brother’s neck, pulling him down into a tender kiss, which Sam returned with just as much gentleness. And when they pulled away, they were both smiling at each other.

“How can I be so damn lucky?” Dean mumbled against Sam’s lips, the younger hunter laughing softly.

“Well, after all the shit that we’ve been through, I guess it was time for something good to happen, right?” he asked, then winked at his grinning older brother.

-

They got back into the car, the rest of the drive to the bunker being peaceful. Sam couldn’t believe that not only did he have sex with his older brother, but that he loved it. He was pretty sure that was the best sex he’s ever had. The silence in the car wasn’t awkward, just blissful, calm, until Dean just had to ruin the nice mood with his cocky comments.

“So,” he said, glancing at Sam from the corner of his eyes, already grinning smugly. “Do you like feeling the smooth satin against your skin, Sammy?” Dean asked, and Sam felt his face flushing in embarrassment. That bastard. He was still feeling a bit hot and bothered from the drug, and Dean’s remarks weren’t helping.

“Shut up. Charlie forced me to wear them,” he said, avoiding eye contact with a surely grinning Dean.

“Yeah right, so you weren’t enjoying it at all, right?” Dean chuckled, the low sound sending a shiver down Sam’s spine and his cock was starting to harden again. Fuck. He shifted in his seat, hoping that Dean wouldn’t notice it and cleared his throat. He did think that it was comfortable, and did like it, but he wasn’t ever going to let Dean know.

“Just because you seem to be having a cross-dressing kink doesn’t mean that I should, too,” Sam mumbled, but when he looked up at Dean, into those beautiful green eyes and that heartwarming smile, Sam gave up. “I’m not going to dress up as a girl just for you,” he said, crossing his arms.

“No need to. The panties are enough.” Dean winked, making Sam feel even more uncomfortable in his skirt. Damn Dean and his…well, everything.

So he decided to have some fun too. “Only if you deserve it,” Sam said as he licked his lips and smirked, making Dean raise an eyebrow, then laugh.

“Oh, so that’s going to be my reward from now on?” He wiggled his eyebrows, smiling widely, and Sam was pretty sure that he hadn’t seen his brother look so happy in months. Maybe even years.

“You know that you love it,” Sam joked, leaning back in his seat and running his fingers through his sweaty hair, slowly and seductively and obviously on purpose.

Dean glanced at Sam, then couldn’t take his eyes off of him. “I do, but that isn’t the only thing I love,” he said quietly, and if Sam didn’t know better, he would have thought that Dean seemed shy. He flashed a dimpled, wholehearted smile at Dean and quickly leaned closer, placing a soft kiss on his jaw, before saying, “Me too.”

And they didn’t have to say it, since they both knew what the other meant. They loved each other, more than brothers, more than lovers, it was a whole new kind of love that only soulmates had. And Sam and Dean Winchester?

They were a match literally made in Heaven, created for each other.

**Notes for the Chapter:**

> And Wincest has been created!

**Author's Note:**

> Wincest shall happen in the next chapter~


End file.
